Synthesis of pyrano[3,2-c]quinoline-4-carboxylates and 2-(4-oxo-1,4-dihydroquinolin-3-yl)fumarates

被引：27
|
作者：
El-Sheref, Essmat M. [1 ]
Aly, Ashraf A. [1 ]
Mourad, Aboul-Fetouh E. [1 ]
Brown, Alan B. [2 ]
Braese, Stefan [3 ]
Bakheet, Momtaz E. M. [1 ]
机构：
[1] Menia Univ, Fac Sci, Chem Dept, El Minia 61519, Egypt
[2] Florida Inst Technol, Chem Dept, 150 W Univ Blvd, Melbourne, FL 32901 USA
[3] Karlsruhe Inst Technol, Inst Organ Chem, D-76131 Karlsruhe, Germany
来源：
CHEMICAL PAPERS | 2018年 / 72卷 / 01期
基金：
美国国家科学基金会;
关键词：
2,4(1H,3H)-Quinolinediones; Dialkyl acetylenedicarboxylates; Pyrano[3,2-c]quinolones; Quinolinofumarates; HIV-1; REVERSE-TRANSCRIPTASE; DRUG-RESISTANCE PROPERTIES; DIMETHYL ACETYLENEDICARBOXYLATE; NONNUCLEOSIDE INHIBITORS; RECEPTOR ANTAGONISTS; DESIGN; HETEROCYCLES; DERIVATIVES; QUINOLINE; ACIDS;
D O I：
10.1007/s11696-017-0269-6
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Reaction of equimolar amounts of 2,4(1H,3H)-quinolinediones and diethyl acetylenedicarboxylate in absolute ethanol, containing catalytic triethylamine, gave ethyl 5,6-dihydro-2,5-dioxo-6,9-disubstituted-2H-pyrano[3,2-c]quinoline-4-carboxylates in good yields. In a different manner, reaction of two equivalents of dialkyl acetylenedicarboxylates with one equivalent of 2,4(1H,3H)-quinolinediones afforded dialkyl 2(4-oxo-1,4-dihydroquinolin-3-yl)fumarates in good yields. The structures of the products were elucidated by H-1 NMR, C-13 NMR, two-dimensional NMR, IR, mass spectra and elemental analyses. [GRAPHICS] .
引用
收藏
页码：181 / 190
页数：10
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